The present invention relates to novel 3-arylphenyl sulfide derivatives and insecticides and miticides containing them as an active ingredient.
East German Patent No. 142541, East German Patent No. 142542, JP-A-7-2655 and Tetrahedron vol. 39, p.2289 (1983) and Tetrahedron Lett. vol. 25, 44, p.5095 (1984) disclose 3-methylthiobiphenyl derivatives, and East German Patent No. 4323916 and International Patent Application WO95/02580 disclose 3-pyridylphenyl sulfide derivatives. However, none of them mention anything about insecticides or miticides. Also, International Patent Application WO96/06830, JP-A-2-184675, JP-A-60-233061, European Patent No. 152590, South African Patent No. 6800955 and German Patent No. 3316300 report 3-azorylphenyl sulfide derivatives but mention nothing about insecticides or miticides. On the other hand, use of 4-biphenyl sulfide derivatives as insecticides is reported, for example, in U.S. Pat. No. 3442955. However, the 3-arylphenyl sulfide derivatives of the present invention have not been known yet.
In recent years, some of the conventional commercial insecticides are restricted in their use in view of problems of persistency, accumulation and environmental pollution, and others have become less effective as the pest insects have acquired resistance during their use for a long period of time. Therefore, it has been desired to develop a new insecticide which is highly effective at a low dose and excellent in safety.
Under these circumstances, the present inventors have synthesized various 3-arylphenyl sulfide derivatives and have studied their physiological activities. As a result, it has been found that the compounds of the present invention exhibit outstanding effects on various pests, especially on farm and garden pests including mites represented by two-spotted spider mite, Kanzawa spider mite and citrus red mite, pest lepidopterans represented by diamondblackmoss, Asiatic rice borer and beat armyworm, pest hemipterans represented by brown rice planthopper, green rice leafhopper and cotton aphid and pest coleoptera represented by adzuki bean weevil. The present invention has been accomplished on the basis of this discovery.
That is, the present invention provides (1) 3-arylphenyl sulfide derivatives represented by general formula (I): 
{ wherein R is a C2-C6 alkyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups), a C2-C6 alkenyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups), a C2-C6 alkynyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups), a C3-C6 cycloalkyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups) or a C4-C9 cycloalkylalkyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups), n is an integer of from 0 to 2, Ar is a group represented by any one of general formulae: 
wherein Q1, Q2, Q3, Q4 and Q5 are, respectively, a nitrogen atom or C-A1, a nitrogen atom or C-A2, a nitrogen atom or C-A3, a nitrogen atom or C-A4, and a nitrogen atom or C-A5, Q6 is an oxygen atom or a sulfur atom, Q7 is a nitrogen atom or C-A7, Q8 is a nitrogen atom or C-A8, A1, A5, A7, A11 and B0 are hydrogen atoms ,halogen atoms, amino groups, cyano groups, nitro groups, C1-C6 alkyl groups, C1-C4 haloalkyl groups, C1-C6 alkylthio groups (which may be mono- or poly-substituted by halogen atoms) or C1-C6 alkoxy groups, A2, A3, A4, A6, A9, B1, B2 and B3 are hydrogen atoms, halogen atoms, cyano groups, nitro groups, C1-C6 alkyl groups (which may be mono- or poly-substituted by halogen atoms, hydroxyl groups, cyano groups, C2-C7 alkoxycarbonyl groups or C1-C6 alkoxy groups), C2-C6 alkenyl groups (which may be mono- or poly-substituted by halogen atoms or cyano groups), C2-C6 alkynyl groups (which may be mono- or poly-substituted by halogen atoms or cyano groups), C1-C6 alkoxy groups (which may be mono- or poly-substituted by halogen atoms, cyano groups, C2-C5 alkoxycarbonyl groups or C1-C3 alkoxy groups), C1-C6 alkylthio groups (which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups), C1-C6 alkylsulfinyl groups (which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups), C1-C6 alkylsulfonyl groups (which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups), C1-C7 acyl groups, C2-C5 haloalkylcarbonyl groups, carboxyl groups, C2-C7 alkoxycarbonyl groups or NR1R2 [wherein R1 and R2 are independently hydrogen atoms, C1-C6 alkyl groups (which may be mono- or poly-substituted by halogen atoms, cyano groups, hydroxyl groups, C1-C6 alkoxy groups or C1-C6 alkylthio groups), C2-C6 alkenyl groups (which may be mono- or poly-substituted by halogen atoms or cyano groups), C2-C6 alkynyl groups (which may be mono- or poly-substituted by halogen atoms or cyano groups), C1-C7 acyl groups or C2-C7 alkoxycarbonyl groups or may form a 5 to 6-membered ring together with the nitrogen atom attached thereto], A8 is a hydrogen atom, a halogen atom, a cyano group, a C1-C6 alkyl group (which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups), a C1-C6 alkoxy group (which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups), a C1-C7 acyl group, a C2-C5 haloalkylcarbonyl group or NR1R2 (wherein R1 and R2 are the same as defined above), and A10 is a hydrogen atom, a C1-C6 alkyl group (which may be mono- or poly-substituted by halogen atoms or C1-C3 alkoxy groups), a C1-C7 acyl group, a C2-C5 haloalkylcarbonyl group, a carboxyl group or a C2-C7 alkoxycarbonyl group; provided that when Ar is represented by general formula (Ar-1) or (Ar-2), not more than three of Q1-Q5 are nitrogen atoms; when Ar is represented by general formula (Ar-1) wherein only Q5 is a nitrogen atom, A1 is a hydrogen atom; when Ar is represented by general formula (Ar-1) wherein Q1, Q2, Q3, Q4 and Q5 are, respectively, C-A1, C-A2, C-A3, C-A4 and C-A5, A21 A3, A4 and B2 are not simultaneously hydrogen atoms; when all of A1 to A5 are hydrogen atoms, compounds wherein B2 is a methyl group, and R is an isopropyl are excluded; and when Ar is represented by general formula (Ar-4) wherein Q8 is C-A8, R is a C2-C6 alkyl group (which may be mono- or poly-substituted by halogen atoms), a C3-C6 cycloalkyl group (which may be mono- or poly-substituted by halogen atoms) or a C4-C9 cycloalkylalkyl group (which may be mono- or poly-substituted by halogen atoms)}, (2) insecticides or miticides containing these 3-arylphenyl sulfide derivatives as an active ingredient (3) a method of killing a farm or garden pest insect or mites which uses an effective amount of these 3-arylphenyl sulfide derivatives.
The terms used in this application are defined below.
The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
The alkyl group means a linear or branched C1-6 alkyl group such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, unless otherwise noted.
The cycloalkyl group means a C3-6 cycloalkyl group such as a cyclopropyl group, a cyclopentyl group or a cyclohexyl group.
The cycloalkylalkyl group means a C1-3 alkyl group substituted with a C3-6 cycloalkyl group such as a cyclopropylmethyl group, a cyclopentylmethyl group or a cyclohexylmethyl group.
The alkenyl group means a linear or branched C2-6 alkenyl group such as an ethenyl group or a 2-propenyl group.
The alkynyl group means a linear or branched C2-6 alkynyl group such as an ethynyl group or a 2-propynyl group.
The haloalkyl group means a C1-4 alkyl group substituted with from 1 to 9 identical or different halogen atoms such as a chloromethyl group, a trifluoromethyl group or a tetrafluoroethyl group, unless otherwise noted.
The alkoxy group means an alkyl-O-group wherein the alkyl moiety is as defined above, such as a methoxy group or an ethoxy group.
The alkoxyalkyl group means an alkyl-O-alkyl-group wherein the alkyl moieties are as defined above, such as a methoxymethyl group or an ethoxymethyl group.
The alkoxyalkoxy group means an alkyl-O-alkyl-O-group wherein the alkyl moieties are as defined above, such as a methoxymethoxy group or an ethoxymethoxy group.
The haloalkoxy group means a haloalkyl-O-group wherein the haloalkyl moiety is as defined above, such as a trifluoromethoxy group or a 2,2,2-trifluoroethoxy group.
The alkylthio group, the alkylsulfinyl group and the alkylsulfonyl group mean, respectively, an alkyl-S-group, an alkyl-SO-group and an alkyl-SO2-group wherein the alkyl moieties are as defined above, such as a methylthio group, an ethylthio group, a methylsulfinyl group, an ethylsulfinyl group, a methylsulfonyl group or an ethylsulfonyl group.
The haloalkylthio group, the haloalkylsulfinyl group and the haloalkylsulfonyl group mean, respectively, a haloalkyl-S-group, a haloalkyl-SO-group and a haloalkyl-SO2-group wherein the haloalkyl moieties are as defined above, such as a trifluoromethylthio group, a dichlorofluoromethylthio group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a trifluoromethylsulfonyl group or a 2,2,2-trifluoroethylsulfonyl group.
The acyl group means a formyl group or an alkyl-CO-group wherein the alkyl group is as defined above, such as an acetyl group or a propionyl group.
The haloalkylcarbonyl group and the alkoxycarbonyl group means, respectively, a haloalkyl-CO-group and an alkoxy-CO-group wherein the haloalkyl and alkoxy moieties are as defined above, such as a trifluoroacetyl group or a methoxycarbonyl group.
Preferred compounds of general formula (I) described above are those wherein Ar is represented by general formula (Ar-1) or general formula (Ar-4), R is a 2,2,2-trifluoroethyl group, a n-propyl group, a 2,2,3,3-tetrafluoropropyl group or a cyclopropylmethyl group, and n is 0 or 1.
Still further preferred compounds are those wherein R is a 2,2,2-trifluoroethyl group, a n-propyl group, a 2,2,3,3-tetrafluoropropyl group or a cyclopropylmethyl group, Ar is a phenyl group having hydrogen atoms as A1 and A5 and a halogen atom, a difluoromethoxy group, a trifluoromethoxy group or a trifluoromethyl group as A3 or A2, B0 is a hydrogen atom, a methyl group or a halogen atom, B2 is a halogen atom, a cyano group, an alkyl group or a haloalkyl group, and n is 0 or 1.
Now, typical specific examples of the compound represented by general formula (I) of the present invention will be given in Tables 1 to 60. The compound numbers used in the tables will be referred to in the subsequent description. Herein, the symbols in the tables denote the following groups.
Me: a methyl group, Et: an ethyl group,
Pr: a n-propyl group, Pr-i: an isopropyl group,
Pr-c: a cyclopropyl group, Bu: a n-butyl group,
Bu-i: an isobutyl group, Bu-s: a sec-butyl group,
Bu-t: a tert-butyl group, Bu-c: a cyclobutyl group,
Pen : a n-pentyl group, Pen-i: an isopentyl group,
Pen-c: a cyclopentyl group, Hex-c: a cyclohexyl group.
The compounds represented by general formula (I) are obtainable by the processes described below, but their production is not restricted to these processes.
 less than Process 1 greater than 
A compound (I) represented by general formula (I) of the present invention having a phenyl group substituted with an RS(O)n group can be obtained by using a 3-arylphenylthiol as the starting material. 
(wherein L1 is a halogen atom, an alkylsulfonyloxy group, a phenylsulfonyloxy group or SO2M, and M is an alkali metal or an alkaline earth metal [preferably sodium or potassium].)
That is, a compound represented by general formula (II) yields a 3-arylphenyl sulfide derivative represented by general formula (I-1) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (III) in from 0.5 to 10 l of a solvent in the presence of from 1 to 5 moles of a base or from 1 to 5 moles of a radical initiator, in relation to 1 mole of the compound represented by general formula (II).
The solvent may, for example, be an ether such as diethyl ether, tetrahydrofuran or dioxane, an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene, a halogenated hydrocarbon such as 5 dichloromethane, chloroform or dichloroethane, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide or sulforane, an alcohol such as methanol, ethanol or isopropyl alcohol, a nitrile such acetonitrile or propionitrile, an ester such as ethyl acetate or ethyl propionate, an aliphatic hydrocarbon such as pentane, hexane, cyclohexane or heptane, a pyridine such as pyridine or picoline or water, or a solvent mixture thereof.
The base may, for example, be an inorganic base, e.g. an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkaline earth metal hydroxide such as calcium hydroxide or magnesium hydroxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate or an alkali metal bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, a metal hydride such as sodium hydride or potassium hydride, a metal salt of an alcohol such as sodium methoxide, sodium ethoxide or potassium tertbutoxide or an organic base such as tiethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine or 1,8-diazabicyclo[5.4.0]-7-undecene.
The radical initiator may, for example, be sulfurous acid, a sulfite salt or a sulfite adduct such as Rongalite (sodium formaldehyde sulfoxylate). The base and the radical initiator may be used together.
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9230xc2x0 C. to the reflux temperature of the reaction system, preferably from 0xc2x0 C. to 150xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound.
 less than Process 2 greater than 
A compound represented by general formula (I-1) of the present invention is also obtainable by using a compound represented by general formula (IV), which is the oxidative dimer of a compound represented by general formula (II) used in Process 1, as the starting material. 
(wherein L2 is a halogen atom or a sulfinate salt, and Ar, B0 to B3 and R are as defined above.)
That is, a compound represented by general formula (IV) yields a 3-arylphenyl sulfide derivative represented by general formula (I-1) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (V) in from 0.5 to 1 l of a solvent in the presence of from 1 to 5 moles of a radical initiator (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (IV).
The solvent may, for example, be an ether such as diethyl ether, tetrahydrofuran or dioxane, an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide or sulforane, a nitrile such acetonitrile or propionitrile, an ester such as ethyl acetate or ethyl propionate, an aliphatic hydrocarbon such as pentane, hexane, cyclohexane or heptane, a pyridine such as pyridine or picoline or water, or a solvent mixture thereof.
The radical initiator may be used in combination with the base described for Process 1.
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9230xc2x0 C. to the reflux temperature of the reaction system, preferably from 0xc2x0 C. to 150xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein L3 is a halogen atom, and Ar is a group represented by general formula (Ar-1) or general formula (Ar-3), and B0 to B3, R and n are the same as defined above.)
That is, a compound represented by general formula (VI) or general formula (VII) yields a 3-arylphenyl sulfide derivative represented by general formula (I) as intended when reacted with from 1 to 2 moles of a metal (such as lithium, magnesium or zinc) or an organometal compound (such as n-butyllithium) in from 0.5 to 10 l of a solvent and then with from 1 to 5 moles of the other compound represented by general formula (VI) or general formula (VII) in the presence or absence of from 0.01 to 1 mole of a transition metal catalyst.
The solvent may, for example, be an ether such as diethyl ether, tetrahydrofuran or dioxane, an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene, an aliphatic hydrocarbon such as pentane, hexane, cyclohexane or heptane, a pyridine such as pyridine or picoline, or a solvent mixture thereof.
The transition metal catalyst may, for example, be a palladium compound such as palladium acetate, dichlorobis(triphenylphosphine) palladium, tetrakis(triphenylphosphine)palladium or tris(dibenzalacetone) palladium or a nickel compound such as bis(triphenylphosphine) nickel chloride or tetrakis(triphenylphosphine) nickel.
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9290xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9278xc2x0 C. to 60xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound.
As L3 as defined above, a bromine atom or an iodine atom is generally preferable, but when the reaction of a compound represented by general formula (VII) with a metal or an organometal compound is followed by treatment with a benzene derivative of general formula (VI) wherein neither A1 nor A5 is a hydrogen atom, L3 is preferably a fluorine atom. 
(wherein Z is a trialkylstannyl group [preferably a trimethylstannyl group], a dihydroxyboranyl group or a dialkoxyboranyl group [preferably a 1,3-dioxobororan-2-yl group or a dimethoxyboranyl group], Ar is a group represented by general formula (Ar-1) or general formula (Ar-3), and B0 to B31 L3 [preferably being a bromine atom or an iodine atom], R and n are the same as defined above.)
That is, a compound represented by general formula (VIII) or (IX) yields a 3-arylphenyl sulfide derivative represented by general formula (I) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (VI) or (VII) in from 0.5 to 10 l of a solvent (as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1) and from 0.01 to 1 mole of a transition metal catalyst (the same as defined for Process 3), in relation to 1 mole of the compound represented by general formula (VIII) or (IX).
When Z mentioned above is a dihydroxyboranyl group, instead of a compound represented by general formula (VIII) or (IX), its dehydrated trimer, which is a boroxine represented by general formula (VIII-1) or (IX-1), may be used. 
RS(O)
(wherein Ar is represented by general formula (Ar-1) or general formula (Ar-3), and B0 to B3, R and n are the same as defined above.)
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9270xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9220xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein Y is a hydrogen atom or a halogen atom, Ar is a group represented by general formula (Ar-1), (Ar-3) or (Ar-4), and L3, B0 to B3, R and n are the same as defined above.)
That is, a compound represented by general formula (X) yields a 3-arylphenyl sulfide derivative represented by general formula (I) as intended when reacted with from 1 to 3 moles of a metal (such as lithium or magnesium) or an organometal compound (such as n-butyllithium) in from 0.5 to 10 l of a solvent (as defined for Process 3) and then with from 1 to 5 moles of a compound represented by general formula (XI) or general formula (XII), in relation to 1 mole of the compound represented by general formula (X).
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9290xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9278xc2x0 C. to 70xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein Ar is a group represented by general formula (Ar-2) or general formula (Ar-4), B4 is an electron-withdrawing group within the above definition of B2 [such as a cyano group, a nitro group or an alkoxycarbonyl group], B0, B1, B3 and R are the same as defined above, and L4 is a halogen atom, an alkylsulfonyloxy group or a phenylsulfonyloxy group.)
That is, a compound represented by general formula (XIII) yields a 3-arylphenyl sulfide derivative represented by general formula (I-2) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XIV) in from 0.5 to 10 l of a solvent in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XIII).
The solvent may be any solvent that does not inhibit the reaction and may, for example, be an aromatic hydrocarbon such as benzene, toluene or xylene, an ether such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane or dioxane, a ketone such as acetone or methyl ethyl ketone, a nitrile such acetonitrile or propionitrile, an aprotic polar solvent such as dimethyl sulfoxide, N,N-dimethylformamide or N,N-dimethylacetamide, an aliphatic hydrocarbon such as pentane, hexane, cyclohexane or heptane, a pyridine such as pyridine or picoline, or a solvent mixture thereof.
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9270xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9220xc2x0 C. to 150xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein Ar is a group represented by general formula (Ar-2) or general formula (Ar-4), and B0 to B3, R and n are the same as defined above.)
That is, a compound represented by general formula (XIII) yields a 3-arylphenyl sulfide derivative represented by general formula (I) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XV) and an anhydrous copper salt (such as anhydrous copper acetate) in from 0.5 to 10 l of a solvent in the presence or absence of from 5 to 50 g of 3 to a 4 xc3x85-molecular sieve in the presence of from 1 to 5 moles of an organic base (such as triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine or 1,8-diazabicyclo[5.4.0]-7-undecene), in relation to 1 mole of the compound represented by general (XIII).
The solvent may be any solvent that does not inhibit the reaction and may, for example, be a haloalkane such as chloroform or dichloromethane, an aromatic hydrocarbon such as benzene, toluene or xylene, an ether such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane or dioxane, a ketone such as acetone or methyl ethyl ketone, a nitrile such as acetonitrile or propionitrile, an aprotic polar solvent such as N,N-dimethylformamide or N,N-dimethylacetamide, an aliphatic hydrocarbon such as pentane, hexane, cyclohexane or heptane, a pyridine such as pyridine or picoline, or a solvent mixture thereof.
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9270xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9220xc2x0 C. to 150xc2x0 C., and completed in from 10 minutes to 72 hours, depending on the compound. 
(wherein Ar is a group represented by any one of general formulae (Ar-1) to (Ar-4), B0 to B3 and R are the same as defined above, L5 is a halogen atom, an alkylsulfonyloxy group, a phenylsulfonyloxy group, an alkylsulfonyl group, a phenylsulfonyl group or a nitro group.)
That is, a compound represented by general formula (XVI) yields a 3-arylphenyl sulfide derivative represented by general formula (I-1) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XVII) (which is also produced from a mineral acid salt of isothiourea having an R group on the sulfur atom as a substituent and an alkali hydroxide or an alkali carbonate) in from 0.5 to 10 l of a solvent in the presence of from 1 to 5 moles of a base, in relation to 1 mole of the compound represented by general (XVI).
The solvent may, for example, be an ether such as diethyl ether, tetrahydrofuran or dioxane, an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide or sulforane, an alcohol such as methanol, ethanol or methyl cellosolve, an aliphatic hydrocarbon such as pentane, hexane, cyclohexane or heptane, a pyridine such as pyridine or picoline or water, or a solvent mixture thereof.
The base may be the base as described for Process 1 or copper monoxide.
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9270xc2x0 C. to the reflux temperature of the reaction system, preferably from 0xc2x0 C. to 150xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein Ar, B0 to B3, R and M are the same as defined above, and m is 0 or 2)
That is, a compound represented by general formula (XVIII) yields a 3-arylphenyl sulfide derivative represented by general formula (I-3) as intended when converted into the diazonium salt in from 0.5 to 10 l of a solvent (the same as defined for Process 1) by a conventional method [using a mineral acid (such as hydrochloric acid or sulfuric acid) and a sulfite salt or an alkyl sulfite] and then reacted with from 1 to 5 moles of a mercaptan salt or a sulfinate salt represented by general formula (XIX), or a disulfide represented by general formula (XX), in relation to 1 mole of the compound represented by general formula (XVIII).
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9230xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9210xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein X1 is a halogen atom, an alkoxy group, an acyloxy group, an alkylsulfonyloxy group or a phenylsulfonyloxy group, Y2 is an alkoxy group or an alkylthio group, L6 is a halogen atom, an acyloxy group, an alkylsulfonyloxy group or a phenylsulfonyloxy group, R1 is an alkyl group, and L3, A8, A10, A11, B0 to B3, R and n are the same as defined above.)
A compound of the present invention represented by general formula (I-4) is also obtainable by a common 1,3-ring-forming dipolar addition reaction (disclosed, for example, in JP-A-63-287768 or Comprehensive Heterocyclic Chemistry vol. 10, p.283), and a compound of the present invention represented by general formula (I-5) is also obtainable by a cyclization reaction with a nitrile derivative (disclosed, for example, in JP-A-1-230562 or Comprehensive Heterocyclic Chemistry vol. 5, p.769).
That is, a compound represented by general formula (XXI) yields a pyrazolylphenyl sulfide derivative represented by general formula (I-4) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XXII), general formula (XXIII) or general formula (XXIV) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XXI).
A compound represented by general formula (XXI) yields a triazolylphenyl sulfide represented by general formula (I-5) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XXV-1) or a compound represented by general formula (XXV-2) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XXI).
Alternatively, a compound represented by general formula (XXI) also yields a triazolylphenyl sulfide represented by general formula (I-5) as intended when converted into an amidrazone (XXI-1) by treatment with from 1 to 3 moles of aqueous ammonia and then reacted in from 0.5 to l10 l of a solvent (the same as defined for Process 1) with an acid halide represented by general formula (XXV-3) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1) or with from 1 to 5 moles of an orthoester represented by general formula (XXV-4) in the presence of from 1 to 5 moles of an acid catalyst (such as a sulfonic acid like p-toluenesulfonic acid or a Lewis acid like titanium tetrachloride), in relation to 1 mole of the compound represented by general formula (XXI).
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9230xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9210xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein L6, R1, X1, A8, A10, A11, B0 to B3, R and n are the same as defined above).
That is, a compound represented by general formula (XXVI) yields a 3-pyrazolylphenyl sulfide derivative represented by general formula (I-4) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XXVII-1) or a compound represented by general formula (XXVII-2) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XXVI).
Also, a compound represented by general formula (XXVI) yields a 3-triazolylphenyl sulfide derivative represented by general formula (I-5) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XXVIII) or a mineral acid salt thereof and compound represented by general formula (XXIX) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XXVI).
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9230xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9210xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein R1, X1, A2 to A5, B0 to B3, R and n are the same as defined above.)
That is, a compound represented by general formula (XXX) yields a 3-(2-oxopyrimidinyl)phenyl sulfide derivative represented by general formula (I-6) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XXVII-3) or a compound represented by general formula (XXVII-4) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XXX).
Also, a compound represented by general formula (XXXI) yields a 3-(6-oxopyrimidinyl)phenyl sulfide derivative represented by general formula (I-7) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XXXII-1) or a compound represented by general formula (XXXII-2) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XXXI).
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9230xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9210xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound. 
(wherein Ar, B0 to B3 and R are the same as defined above and q is 1 or 2)
That is, a compound of the present invention represented by general formula (I-1) yields a 3-arylphenyl sulfide derivative represented by general formula (I-8) as intended when oxidized with from 1 to 6 moles of an oxidizing agent in from 0.5 to 10 l of a solvent, optionally in the presence of a catalyst (such as sodium tungstate), in relation to 1 mole of the compound represented by general formula (I-1).
The oxidizing agent may, for example, be hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (trade name, manufactured by E.I. du Pont; containing potassium hydrogenperoxosulfate), N-chlorosuccinimide, N-bromosuccinimide, hypochlorous acid, tert-butylsodium or sodium hypochlorite.
The solvent may, for example, be an ether such as diethyl ether, tetrahydrofuran or dioxane, an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide or sulforane, an alcohol such as methanol, ethanol or isopropyl alcohol, a halogenated hydrocarbon such as methylene chloride, chloroform or dichloroethane, an aliphatic hydrocarbon such as pentane, hexane, cyclohexane or heptane, a ketone such as acetone, methyl ethyl ketone or cyclohexanone, acetic acid or water, or a solvent mixture thereof.
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9230xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9210xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound.
Compounds of the present invention represented by general formula (I) are obtainable by using other compounds of the present invention, as in Process 13. Namely, a compound of the present invention represented by general formula (I) can be obtained from another compound of the present invention by introducing or converting a functional group by generally known methods (see Examples 13 to 17; however, such processes are not limited thereto).
Now, syntheses of the precursors of the compounds of the present invention are described below in detail.
 less than Process 14 greater than  Syntheses of Precursors Represented by General Formulae (II) and (IV)
Compound represented by general formulae (II) and (IV) can be synthesized as follows and are interconvertible through oxidation-reduction reaction. Especially, a compound represented by general formula (II) can be easily oxidized by atmospheric oxygen into a compound represented by general formula (IV). 
(wherein R2 is a methyl group or a trifluoromethyl group, and Ar, B0 to B3 and Y1 are the same as defined above.)
That is, a compound represented by general formula (XXXIII) yields a compound represented by general formula (II) or (IV) as intended after oxidation into a methyl sulfoxide in from 0.5 to 10 l of a solvent (the same as defined for Process 13) with from 1 to 3 moles of an oxidizing agent (the same as defined for Process 13) followed by the Pummere rearrangement reaction into the corresponding alkyloxymethyl sulfide (XXIV) with from 1 to 5 moles of acetic anhydride or trifluoroacetic anhydride and hydrolysis, in relation to the compound represented by general formula (XXXIII).
Also, a compound represented by general formula (XXXV) yields a precursor represented by general formula (II) as intended when converted into a sulfonyl chloride (XXXVI) with from 1 to 5 moles of chlorosulfonic acid and reduced with from 1 to 5 moles of lithium aluminum hydride, zinc and an acid, tin and an acid or red phosphorus and iodine, in relation to 1 mole of the compound represented by general formula (XXXV).
Further, a compound represented by general formula (XXXV) yields a precursor represented by general formula (IV) when reacted with from 0.4 to 1.0 mole of sulfur monochloride in from 0.5 to 10 l of an inert solvent such as carbon disulfide, nitrobenzene or o-dichlorobenzene in the presence of from 0.01 to 2.0 moles of a Lewis acid such as aluminum chloride, in relation to 1 mole of the compound represented by general formula (XXXV).
Still further, a compound represented by general formula (X) yields a compound represented by general formula (II) as intended when treated with from 1 to 3 moles of a metal or an organometal compound (the same as defined for Process 3) in from 0.5 to 10 l of a solvent (the same as defined for Process 3) and then reacted with from 1 to 5 moles of sulfur, in relation to 1 mole of the compound represented by general formula (X).
Also, a compound represented by general formula (XVIII) yields a compound represented by general formula (II) as intended after conversion into the diazonium salt as in Process 9 and treatment with from 1 to 3 moles of a xanthate salt or a thiocyanate salt followed by alkali hydrolysis.
Each reaction is carried out at an arbitrary temperature within the range of from xe2x88x9270xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9220xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound.
Further, when B2 is an electron-withdrawing group, B4, a precursor represented by general formula (II-1) is available by substitution reaction. 
(wherein Ar, L5 and B0 to B4 are the same as defined above.)
That is, a compound represented by general formula (XXXVII) yields a 3-arylphenylthiol represented by general formula (II-1) as intended when reacted with from 1 to 3 moles of sodium sulfate (XXXVIII) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XXXVII), and then neutralized with a mineral acid or the like.
The reaction is carried out at an arbitrary temperature within the range of from xe2x88x9230xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9220xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound.
Compounds represented by general formulae (X), (XVIII), (XXXIII), (XXXV) and (XXXVII) are obtainable by processes similar to Process 3, Process 4, Process 6, Process 7, Process 10, Process 11 or Process 12, and compounds represented by general formula (X) wherein Y1 is a halogen atom, can obtained by halogenation of the corresponding compound wherein Y1 is a hydrogen.
 less than Process 15 greater than  Synthesis of Precursors Represented by General Formula (XIII) 
(wherein R3 is a hydrogen atom or an alkyl group, and A2 to A11, R1, X1 and L6 are the same as defined above.)
That is, a compound represented by general formula (XXXIX) yields a precursor represented by general formula (XIII-1) as intended after oxidization into an N-oxide (XL) with from 1 to 3 moles of a peracid (such as m-chloroperbenzoic acid or peroxysulfuric acid) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) and treatment with from 1 to 5 moles of an acid halide (such as acetyl chloride or phosphorus oxychloride) followed by hydrolysis under alkaline or acidic conditions, in relation to 1 mole of the compound represented by general formula (XXXIX).
Urea (XLI) yields a precursor represented by general formula (XIII-2) as intended when reacted with from 0.5 to 5 moles of a compound represented by general formula (XXVII-3) or a compound represented by general formula (XXVII-4) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 0.5 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of urea (XLI).
A compound represented by general formula (XLII) yields a precursor represented by general formula (XIII-3) as intended when reacted with from 1 to 5 moles of a compound represented by general formula (XXXII-1) or a compound represented by general formula (XXXII-2) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of the compound represented by general formula (XLII).
Hydrazine hydrate (XLIII) yields a precursor represented by general formula (XIII-4) as intended when reacted with from 0.5 to 5 moles of a compound represented by general formula (XLIV) in from 0.5 to 10 l of a solvent (the same as defined for Process 1), in relation to 1 mole of hydrazine hydrate (XLIII).
Also, hydrazine hydrate (XLIII) yields a precursor represented by general formula (XIII-5) as intended when reacted with from 0.5 to 5 moles of a compound represented by general formula (XXVII-1) or a compound represented by general formula (XXVII-2) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 0.5 to 5 moles of a base (the same as defined for Process 1), in relation to hydrazine hydrate (XLIII).
Further, hydrazine hydrate (XLIII) yields a precursor represented by general formula (XIII-6) as intended when reacted with from 0.5 to 5 moles of a compound represented by general formula (XXVIII) or a mineral acid salt thereof or a compound represented by general formula(XXIX) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 0.5 to 5 moles of a base (the same as defined for Process 1), in relation to 1 mole of hydrazine hydrate (XLIII).
Each reaction is carried out at an arbitrary temperature within the range of from xe2x88x9270xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9220xc2x0 C. to 100xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound.
 less than Process 16 greater than  Synthesis of Precursors Represented by General Formula (XXI) 
(wherein L3, L6, A10, B0 to B3, R and n are as defined above.)
That is, a phenylhydrazine derivative represented by general formula (XLV) yields a compound represented by general formula (XXI) as intended when acylated into a compound represented by general formula (XLVII) with from 1 to 5 moles of a compound represented by general formula (XLVI) in from 0.5 to 10 l of a solvent (the same as defined for Process 1) in the presence of from 1 to 5 moles of a base (the same as defined for Process 1) and then treated with from 1 to 5 moles of a halogenating agent (such as phosphorus trichloride, phosphorus tribromide, thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, triphenylphosphine/carbon tetrachloride or triphenylphosphine/carbon tetrabromide), in relation to 1 mole of the phenylhydrazine derivative represented by general formula (XLV).
Also, a phenylhydrazine derivative represented by general formula (XLV) yields a compound represented by general formula (XXI) as intended when converted into a phenyl hydrazone derivative represented by general formula (XLIX) by treatment with from 1 to 5 moles of an aldehyde derivative or an aldehyde-lower alcohol adduct (an aldehyde hemi-acetal) represented by general formula (XLVIII) in from 0.5 to 10 l of a solvent (the same as defined for Process 3) in the presence or absence of an acid catalyst (such as a sulfonic acid like p-toluenesulfonic acid or a Lewis acid like titanium tetrachloride) and then treated with from 1 to 5 moles of a halogenating agent (such as chlorine, N-chlorosuccinimide, N-bromosuccinimide or tert-butyl hypochlorite).
Each reaction is carried out at an arbitrary temperature within the range of from xe2x88x9270xc2x0 C. to the reflux temperature of the reaction system, preferably from xe2x88x9220xc2x0 C. to 150xc2x0 C., and completed in from 10 minutes to 20 hours, depending on the compound.